Our friend AP joins the show to discuss his nomadic journey, living month-to-month in 23+ cities throughout the United States. Highlights include:

• Pacific Northwest - Best vs worst months, and a creepy landlord who lived in his Portland basement.
• Cali Vibes: San Jose, San Diego, Huntington Beach, and how the ocean is actually cold vs the warmer Caribbean/Gulf
• Scottsdale - The full story on Jack and Steve’s criminally bad golf game, Scottsdale’s housing prices, best restaurants, and “going out” culture.
• Florida - The genesis of our nomad journey, getting caught in BLM and Trump rallies, trying to rent a street-legal golf cart or vespa, and learning the cultural and weather differences between North Florida and South Florida.
• Austin & Lake Travis - Imposter syndrome when staying in Airbnbs that are too nice.
• East Coast - Why Brooklyn was AP’s favorite stop, how a bad Airbnb experience ruined his time in the charming city of Charleston, and other common Airbnb shortcomings.
• Key West - AP details a story that involves ordering condoms from GoPuff and Jack getting locked out of an Airbnb while getting eaten alive by bugs.
• We also further plan our trip to Jamaica that’s totally gonna happen, as well as other potential island trips to Cuba or the Bahamas.

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Steve and Jack crack open their ultimate travel bucket lists and dream big. From chasing the Northern Lights at the most inopportune time of year, to smoking weak joints in Jamaica, to dodging anacondas in the Amazon Rainforest—the places may not have the best wifi. The guys also imagine first-class train rides in Siberia, cold plunges in Antarctica, and lemur-filled wanderings across Madagascar. Along the way, they sprinkle in quirky facts, cultural tidbits, and what they consider to be jokes.

Whether you’re building your own nomad wishlist or just want to escape into a world of wild travel dreams, this episode will surely spark some dumb ideas.

This week we’re taking you to Montreal, Canada’s second-largest city and one of the most unique cultural blends in North America. We break down the numbers behind the city’s size and metro population, then dive into what makes Montreal feel like a mix of Europe and North America all at once. From street dance battles to furry conventions, it truly earns its reputation as a festival city.

Of course, we had to talk food — poutine (in all its variations), foie gras, maple syrup, and why Montreal bagels might ruin New York bagels for you forever. We also hit on the city’s must-see spots, the role of French in everyday life, how bilingual the locals really are, and whether separatist politics still show up in the vibe of the city.

Finally, in this week’s Nomad Hack, we share an unbelievable travel deal: Japan Airlines is giving away free domestic flights within Japan to international travelers. Yes, free. We’ll explain who’s eligible and how to take advantage of it.

If you’ve ever wondered why Montreal speaks French, whether you can get by without knowing it, or if free flights in Japan are really a thing — this episode’s for you.

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We discuss our experiences traveling to Queens, New York for the U.S. Open - Including the legendary Honey Duece cocktail, the longest tennis match ever, and more.

Nomad Hacks: We reveal 5 ChatGPT prompts that could help you find the cheapest hidden flight prices.

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Today we chat with Ken Krell, the founder of location-independent businesses and newsletters including The PrideNomad Letter and The Daily Hug. With years of digital nomad experience, a few thousand LGBTQ+ readers, and a lifetime of stories about building a borderless life as a queer traveler. We find out if this publisher of The Daily HUG is really a daily THUG. (Just kidding, he’s lovely.)

We talk about what it means to belong anywhere, how to make money on the move, why community matters, and the weirdest places Ken’s ever worked from. This episode is equal parts hilarious, heartwarming, and wildly inspiring.

Check out MyDailyHug.com and PrideNomad.com - or follow @ken.krell on Instagram for more!

You're not gonna wanna miss this one. We talk all about the city-state of Singapore, including how it’s half covered in green space, has the best airport in the world, and why it’s nicknamed the City of Lions. We also discuss the “City of Fines” nickname: a deep dive into the country’s bizarre laws, heavy surveillance, and their painful form of punishment called “caning” that involves spanking someone with a cane until they bleed…and bleed some more. Find out why you REALLY don’t want to do drugs or commit vandalism in Singapore in this epic episode.

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Today we discuss what it would be like to live as a digital nomad throughout different points in history. We focus on Ancient Egypt and 18th-century Caribbean, and we even bring on some special guests from these eras to hear about their experiences firsthand.

We start off talking Captain Underpants, why Quebec might be considered part of Latin America, maple syrup-based hot sauce, Goth Babe, and nomading in the past. (0:00-14:30)

Interview with Captain Tobias Copy-Paste, an 18th-century pirate, to talk about casual mutiny, working with parrots, sexually-excited monkeys, messages in a bottle, eyepatches vs Fetty Wap, staying hydrated at sea, and more. (14:30-29:50)

Tying it back to the current situation in Haiti, a Cuban-American immigrant who’s super against any further Cuban immigration in the US, why some Latinos don’t like Miami, and owning an alligator as a pet. (29:50-34:30)

Interview with Khamet, an Egyptian stone carver from 2500 BC…E discussing using the sun as a clock, why multiple gods are better than one god, why LinkedIn lingo is the worst, ancient wifi aka pigeon-fi, being careful bartering with priests, and how to make artwork go viral. (34:30-01:01:33)

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Personal Updates: the guys discuss their recent travels to Montreal and Denver, and why Montreal is such an underrated city. (0:00-3:30)

Nomad News: TSA says sweating in this particular area can set off the alarms. We give you the inside scoop, discuss a personal story about getting a hardcore bag search, and tie it all back to our favorite terrorist failure, the shoe bomber. (3:30-10:20)

Nomad News: a growing trend in the travel world with personalized, pay-to-play recommendation apps like Places and AmiGo. Why are Millennials and Gen Z ditching TripAdvisor and AI listicles for tastemaker-curated guides? Is knowing about a hidden ramen joint in Tokyo the new Gucci belt? And would you pay $129 a year just to know where the cool people eat? (10:20-21:35)